The Strip Club
by morgana07
Summary: 1-shot. A multi-time piece. Caleb takes Sam to someplace he really shouldn't while watching him then learns years later that forgetting that mistake might not be as easy as he thought it would be.*Some teen!chester. Upset/confused/good!Sam / Not thinking/then overthinking!Caleb & some frustrated/angry/nig brother!Dean. *See Author note for more*


**The Strip Club**

**Summary: **_1-shot. A multi-time piece. Caleb takes Sam to someplace he really shouldn't while watching him then learns years later that forgetting that mistake might not be as easy as he thought it would be.*Some teen!chester. Upset/confused/good!Sam / Not thinking/then overthinking!Caleb & some frustrated/angry/nig brother!Dean. *See Author note for more*_

**Warnings/Spoilers: **_Okay, this is tricky to warn for but here goes: Language as it includes some minor swearing but it also contains some mild descriptive scenes. Nothing serious as I leave it more up to the imagination of the reader but I'll still warn for it. No spoilers even though the last segment takes place during the current season._

**Tags: **_None._

**Disclaimer: **_I don't own anything. This is merely for entertainment._

**Author Note: **_In a couple other stories, especially in 'Fevered' I mentioned Caleb taking Sam to his first strip club at fourteen (yes, I'm aware of the legalities of that) so after a couple requests this is what came up. It starts out in teen!chester land then moves to pre-season to see just what Sam took from his night out with Caleb to finally the most current season and after 08x21 The Great Escapist. I tried to keep the descriptions down and leave it to you guys to imagine the rest but bear with me since this one went a little beyond my comfort range. Enjoy._

**SPN SPN SPN SPN**

**1997, Texas:**

"Okay, listen up and listen good. His bedtime is no later than 10:00, no sugar after 8:00…no, forget that. He doesn't see anything with sugar until I'm back. He needs to practice with shooting but since I don't trust you with a gun half the time I sure as hell am not trusting you with a gun and my baby brother so…"

Caleb rolled his eyes while trying not to snicker at the way his friend was behaving, especially since while it was amusing to him it was not as amusing to Dean Winchester who'd still been snarling when the other hunter arrived at the run down motel that the Winchesters were calling home this week.

"Ace, it's not like when Sam was little and we'd watch him. The kid is fourteen and…" he sighed when a sharp finger poked him square in the chest and a pair of hot green eyes practically bored into his.

"Exactly. He's fourteen years old and Sam's trying to stretch the boundaries," Dean glanced over at his younger brother who was listening to the final orders their father was giving him. "So we're going by my rules which means no sugar, no guns, no knives, no parties and I'm aiming that one at you and," to make certain he was fully understood, the eighteen year old hunter stepped fully into his friend's space. "…and no porn crap."

At nineteen, Caleb was a year older than the older Winchester son which often made him and Dean partners in crime when they were allowed to hunt solo and the bald young hunter knew Dean was more than into the stuff that Caleb liked to enjoy…at least he was usually.

Dean was willing to go to places that Caleb knew John Winchester would kill them both over if he ever learned about it and he was willing to try things but since Dean was going on a hunt with John and that left Caleb in charge of Sam the rules had changed dramatically.

"What are the rules for after Sammy goes to sleep?" he decided to test the waters and groaned more when the finger poked him again, only harder. "Dean…"

"Those are the rules until I get back which should be tomorrow night," Dean hated this idea so much that he'd even got in his Dad's face about just letting Caleb go in his place but that set John off on the rant that he babied Sam too much and it would do Sam good to be around someone else. "It's less than forty-eight hours, dude. Even you can go without porn or other crap for that long."

Caleb rubbed a hand over his shaved head. He knew he could. That wasn't the issue he had with Dean's rules. His issue was that he thought that perhaps John was right on certain things. His friend was more protective of the younger Winchester than their father ever had been.

However he wasn't stupid enough to directly say that to Dean's face since he'd seen the way Dean could get when it came to protecting Sam and he'd be damned if he'd start this babysitting job out with his face busted open.

"Okay, okay, I get it," he finally conceded, looking down at the small and clearly disgusted huff was heard and noticed the scowl Sam was shooting his brother. "I take it he's not thrilled with this plan either?"

"I'm fourteen. I don't need Caleb watching over me like I was a baby," Sam argued, fighting the urge to pout since that wouldn't go very well with his 'I'm old enough to stay on my own' argument. "Why can't I just come with you?"

Giving a look toward where John was standing by the door, Dean read the slight shake of his head and sighed. "You've still got that cough, Sam," he knew that was the main excuse their Dad was using to keep Sam from coming but the real reason was that John didn't know how dangerous this hunt would get and didn't want to expose Sam to risk if they could help it.

"So you get to hang out here with Caleb. You can read, play some games…do not let him play poker with you cause he cheats and Dad and I'll be back by tomorrow night," he finished, not missing the war going on in his little brother's hazel eyes as Sam fought between tears and anger. "Sammy, y'know I'd take you in a heartbeat but…"

"We don't need this stick in the mud to have fun, Sam," Caleb broke in, giving his friend a way out since he knew how close to breaking Dean was and if Sam turned on his fabled puppy eyes that this would turn into an all-out fight between Dean and John. "Pizza, soda…okay, juice, God, I hate you right now, Dean."

"You won't if you have to deal with him on a sugar high," Dean chuckled, hearing John call and swearing this had better be one damn short hunt as he knelt down so he'd be more on Sam's level even though his brother had started to get taller it seemed each day. "Listen to Caleb and call me if there's any issue," he urged, lightly squeezing the side of his brother's neck in a way of reassuring Sam that this would work out. "You watch him."

Caleb waited until the taillights of the Impala were out of sight to finally let out the breath he'd been holding, then glanced down at a clearly unhappy Sam. "Hey, John's left you with Jim and Bobby which can't be any worse than getting stuck with me, Sammy," he decided that out of the three of them he had to be a better choice.

"Sam," came the automatic correction since only Dean could call him that usually and even then Sam would offer up the correction though mainly just to annoy his brother. "I'm going to go read or…something," he decided, figuring he may as well do research on something or just read one of the new sci-fi books Dean had bought him.

Hearing the soft click of the other bedroom door gave Caleb a chance to rethink his idea of agreeing to John's plan to stay with Sam, especially since he was really limited on what he could do now that Dean had laid down the rules.

A quick run through the motel TV told the hunter just how serious his friend had been when he found all the more 'interesting' stations locked. "Damn it, Dean," he groaned, not really believing his friend had been serious about that rule.

Having hunted with the Winchesters before, Caleb knew what type of food John normally bought but as he rummaged through the refrigerator and cabinets he let out a stronger more vocal curse this time. "This is beyond drastic now, Ace."

A look at the selection of food gave him a choice of some precooked dinners, fruit, vegetables, water and juice. No junk food, no soda, no beer. Even the precooked stuff had a healthy tone to them and Caleb knew damn well that Dean wouldn't ever touch half this stuff so it had been bought to go with Dean's 'rules of Sammy-sitting'.

Taking a peek in at Sam told Caleb that the younger boy was totally absorbed in the world of the book he was holding and this didn't seem right to him.

Sam was fourteen and more at home with computers, libraries and research which just seemed weird and unnatural to Caleb who still recalled his teenage years as well as the trouble he and Dean could get into at the age.

Pacing the living room while trying to find something on TV, Caleb finally gave up on that idea when another plan began to bloom in his mind and he battled with his conscious for all of ten seconds before letting out a shout for Sam.

"Yeah?" Sam still held the book in his hand, his finger marking the page he'd been on only to blink when his jacket was tossed at him. "Huh? Caleb, what're you…?"

"We're going out to get some real food and then I'm going to enlighten your world with some culture and entertainment," the hunter responded while snatching up his keys and nudging the suddenly more cautious teenager out to his car. "Sam, trust me. Didn't I say we'd have fun while your Dad and Dean were gone?"

Sam might've been fourteen but he wasn't stupid. He'd grown up around Caleb and he knew more than anyone else the kinds of things he and Dean could and have gotten into so he wasn't sure if his idea of fun would be in line with Caleb's.

He was about ready to argue and just stay at the motel when suddenly Sam's more rebellious teenage side surfaced.

Ever since he'd turned thirteen, Sam had been trying to get both his Dad and Dean to give him a bit more leeway but it seemed the older he got the tighter his Dad tried to hold on and he doubted if his brother would ever back off, not that he minded that since he knew Dean was more prepared as a hunter than Sam ever wanted to be.

There were times when Sam felt smothered and just wanted a chance to be more normal, to be treated like a regular teenager and while he felt a little scared he also knew that Caleb wouldn't do anything to bring him into direct danger…or else Dean would kill him.

The stop at the diner wasn't anything new since for Sam diners and fast food joints were where they basically always ate. Watching Caleb flirt with the waitresses made him roll his eyes behind his burger because he'd grown up with Dean and his brother was a master flirter.

Dean, as Sam had seen, could draw attention just by smiling and when he deliberately turned on the charm it often took all Sam had not to gag but watching Caleb try the same moves was kind of funny to him because the older man just didn't have the same charisma and charm that Dean did and wondered if he should point out that Dean could probably offer some lessons if Caleb was interested.

"Must have a guy already," Caleb decided when the waitress smiled but just as easily brushed off the flirtations as if he hadn't even been trying. "Her loss, kid."

Giving a simple nod while munching on his food, Sam was glad his mouth was full so he didn't have a chance to correct Caleb since he'd seen Dean flirt with the same girl just not two nights earlier and he hadn't seen his brother for several hours so having a guy didn't seem to be the problem.

So far hanging out with Caleb hadn't been so bad and Sam was just on the verge of thinking that he could handle it since it was a little like being with Dean but he just had to work a little harder on making certain Caleb stayed out of trouble.

"Alright, dinner's done. Now we hit the main attraction," Caleb had been in this area before and so knew where he was driving while looking next to him with a slight frown. "Getting you in may be a little iffy but I know the owner so it shouldn't be a huge problem…if a little illegal."

"Huh?" Sam's eyes jumped at that and he was just about to ask what the hell Caleb was up to when his already wide eyes nearly jumped out of his head and he suddenly had a small ball of insecurity curl in his belly. "Umm, this is so against Dean's rules," he warned, knowing it had to be.

He'd been going over that list of rules all night until he was fairly certain that he'd found a loophole that he could, if Dean ever learned of this, use to save his skin.

"Actually, Ace said no porn on the TV. He didn't say I couldn't take you if I went out and he didn't say no strip clubs," Caleb smirked, pleased that he'd been able to get around that one but he didn't miss the look of pure confused panic in those huge hazel eyes that were watching him. "Sam, it's just a club with dancers…who do certain things. No biggie."

"If it's not a biggie why's it illegal for me?" Sam tossed back, knowing what a strip club was but also knowing this one, by the name on the building, seemed to be a bit more.

Running his tongue over his teeth on that little question, Caleb was reminded that Sam was the smarter one of John's sons, at least where the big things were concerned and chose honesty for this one. "You normally have to be of legal age. Dean and I can fake it but you, with those big eyes and fluffy hair, are gonna be hard to fake it so I might have to resort to bribery."

"Caleb, maybe I should stay in the car while you go…" Sam wasn't sure what exactly Caleb or Dean for that matter did when they went to places like this and he certainly really didn't need the imagery either.

"Nope, I promised I'd watch you and that's what I'm doing," Caleb pulled a ball cap out of the backseat to tug it onto Sam's head. "Besides, I feel like it's my duty to introduce you to certain things in this world that I know your Dad sure as Hell never will and…I doubt if Dean would since he's stuck on this little brother thing," he knew as well as he knew himself that his friend would swallow his tongue before ever taking Sam to a strip club.

Curiosity high, Sam still felt that knot in his belly tighten and also felt like he was betraying his big brother by doing something with Caleb that he probably should be doing with Dean…in a few more years.

Loud sounds, bright lights, strong smells all assaulted his senses the moment Caleb opened the first set of doors. Keeping a tight hand on Sam so he didn't lose the kid, he blew out a breath when he caught sight of the woman headed his way. "Ruthie!"

Sam had to look way up to see the woman's face and swallowed. She was taller than even his Dad so that put her really above Caleb.

Wild red hair spilled everywhere but didn't do a thing to cover the massive breasts that seemed ready to spill out of the tight dress she wore that hide nothing and showed more than Sam really felt at ease seeing.

"Well, look at what the wildcat dragged in," she laughed with a heavy Texas accent as she reached with strong arms to lift the hunter off the floor in a hard hug. "Little Caleb. Where's your pal that you had the last time?"

Struggling to get his breath back as he was set back on the floor, Caleb shook his head. "Dean's not with me this trip, Ruth," he chuckled at her pout then glanced at Sam. "I'm watching over his brother though so…we need to maybe come to some sort of…deal?"

Dropping a look down, bright blue eyes seemed to look right through Sam until he felt like squirming when he fought to groan at a hand with long painted nails ruffled through his hair.

"How old is he, Caleb?" she asked, taking another long look before nodding. "He can't be more than fourteen, boy! What in the hell are you thinking bringing him here?"

That's what Sam was wondering but didn't have the breath in his lungs to answer as he caught sight of something going on out in the main room.

"I have him until Dean and their Dad get back, Ruthie. Sam's fourteen and needs to…experience the finer things in life," Caleb knew that wasn't going to work and so reached into his pocket. "I know he's underage and I know it's illegal as hell but I also know he's not the first underage kid who has snuck through the back door just to watch a couple shows.

"Sara Lynn is working tonight so I know you'll be here longer than a few shows, sugar," Ruthie eyed Sam again then over at Caleb while slipping the two bills he held out down into the bosom of her dress before nodding. "Take one of the back tables but if you take off with Sara Lynn you be sure he's alright or I'll tan your ass."

"Promises, promises," Caleb grinned then led Sam toward the back of the room to a table that was in the shadows but still had a clear view of the stage and the dancers. "Do I need to mention that telling Dean or your Dad about this probably wouldn't be a good plan?"

He hadn't thought of that one since Sam was basically still naïve and too damn honest about things so he hadn't figured on this getting back to his mentor and friend via Sam's innocent babbling.

Scooting to the back of the rounded booth, Sam's eyes looked huge even in the shadows as he took a look at the stage and array of dancers out there then he slowly turned to eye Caleb. "Are they…prostitutes or dancers?"

"Aw geez, kid," Caleb groaned, looking around but the music was too loud for that little question to have been heard. "Ruthie's girls are dancers…though a couple of them may do a little more…after shift. Though they do private dances in the back which is…Hello there, Sara Lynn."

The woman who had drawn Caleb's attention as she stepped up to the table also caught Sam's attention and he suddenly had a better idea of just what kind of culture Caleb had wanted to introduce him to and swallowed.

Sara Lynn looked to be about twenty-something with long sandy blond hair, brilliant green eyes with a dimple on one side when she smiled.

A look out of the corner of his eye since he suddenly had found a string on his jacket interesting told Sam that it probably wasn't her smile that caught the most attention as he was finding it hard to keep his eyes from noticing the way the sheerness of her short outfit seemed to move as she leaned down closer to Caleb while those green eyes slid over to Sam.

"Your friend's cute," she all but purred it then laughed when Sam seemed to pale. "I bet he grows tall and big with the way he seems to be growing into those legs and hands," she reached over to lift one of the teen's hands in hers and smiled fully while winking. "You look me up when you're all grown up, sweetie and I bet I can give you a job in the show I plan on running after I leave here."

Sam's tongue had dried up and his brain was shooting warnings left and right while he struggled to remember to breathe when Caleb finally broke in.

"Hey, his brother will kill me if you give the kid a stroke, Sara," he argued, feeling the tension in Sam but lost his inner battle of common sense when the dancer leaned over to whisper something in his ear while running a not so subtle finger down his thigh. "Ummm, Sam…you sit right here and drink some water or pop and…I'll be right back."

Just getting his breathing back, Sam thought he'd heard wrong until he realized that Caleb had strolled off toward the smaller back rooms for what he guessed would be a private dance with the blond dancer.

He considered briefly calling his brother but just as quickly discarded the idea because he couldn't cover the loud music and noises from the stage as the customers shouted when a particularly leggy brunette stepped out onto the stage dressed only in two skimpy pieces of red leather.

"Man, Dean will kill Caleb," he breathed, deciding that he could handle this for the little bit that Caleb had said they'd be in the club. "I'm not a little kid."

Sam wasn't a baby anymore and he'd seen a couple of the magazines that he doubted his Dad knew Dean had in the bottom of his duffel so he'd seen naked women before. Watching the strippers on the stage wouldn't be any different or so he thought until the brunette began doing some things on that pole in the middle of the stage that Sam didn't think possible.

Looking away from the stage, his hazel eyes kept shifting back to the woman dancing when his eyes went huge as she clung to the pole with her legs then flipped up so that her hands were on the stage while smiling at the men sitting in front of it.

Biting his lip, Sam shifted more in the booth as he was suddenly feeling a bit more than unease and not all of it was in his stomach and he felt his breath hitch. "Crap," he whispered, beginning to feel the same tightness in between his legs as he did that one time he'd spent a bit too much time with that one magazine.

Not wanting the same results tonight, Sam was about to ease out of the booth and go sit in the car when the bottom of the outfit was tugged free while the dancer was still hooked to the pole then she pulled a red leather device out of a box on the stage and the fourteen year old felt like his eyes were going to literally bug out of his head.

"Chantelle can do some really wicked things with those toys," Ruthie had come up to sit in the booth as if noticing that Sam's so-called 'guardian' had vanished like she knew he would. "You know what those things are, honey?"

It took Sam several seconds of swallowing before he trusted his voice wouldn't be a squeak as he couldn't help but watch what the dancer did with her assortment of toys and figured that if this is what his brother and Caleb did while not hunting then he could understand why Dean was so testy when John went along with them. "Um, no."

"Well, you're a little young to know about those whips or toys but since I don't allow touching unless they're on their own time, some of the girls resort to little tricks to help please the customers," Ruthie laughed at the boy's look then tousled his hair again. "You're gonna be a sweet one, sugar and if you grow up to be anything like your big brother then you're also going to grow up drop dead gorgeous."

The blush was instant and hot as Sam felt his cheeks grow warm. He'd seen other women ogling his brother and knew that Dean thought himself a lady killer but Sam couldn't see himself in that category much less earning the same kind of smiles and sidelong looks Dean often received when they were out.

Rubbing his suddenly sweaty hands on his jeans, Sam heard a groan as the brunette on the stage wrapped her legs around the pole then twisted down on it and blinked when he suddenly realized he was the one who'd groaned and felt the blush getting hotter.

Sam lost track of how long he was alone in the booth but he knew that each dancer performed about a half an hour to forty minutes per set and he'd seen about six different women doing things that he knew he'd never understand on that pole, on the stage and on a couple different props that nearly had the fourteen year old calling it quits and reaching for his phone.

"Shit, shit, shit!" Caleb hadn't meant to spend that much time with Sara Lynn, leaving Sam alone out in the club. He knew the kid was basically innocent of all things female except for those occasional peeks at the magazines he'd given Dean one time.

It was only after she was done doing one hell of a crazy dance routine that had sent his every nerve ending to tingling that Sara had told him some of the other dancers working this evening and a quick stroll through his memory soon told the hunter that (A) he needed to spend a lot more time hunting in this neck of the woods and (B) Dean Winchester was going to end him because he'd left his innocent baby brother alone for way too long in a strip club with some dancers that he knew could do some wicked things.

"Sam?" stepping to the table, Caleb felt his already tight nerves nearly explode when the boy wasn't in the booth and various scenes of pain, agony and torture shot through his mind because if Dean didn't kill him then John sure as hell would…or a call to Pastor Jim Murphy would result in a ten hour lecture on morality which would be worse than letting Dean kill him. "Shit!"

"Ruthie took the little cutie into her office," a teddy wearing waitress informed him as she passed on her way to deliver drinks. "I think Melinda's little performance was a bit too much for him."

"I'm dead," Caleb decided, rubbing the back of his neck before heading to the main office on the second floor. "I lost track of time, Ruth and…ow! Hey! Don't your customers have to pay extra for this kind of treatment? Ow!" he shouted at the continued beating by a leather paddle. "Okay, I give in!"

Ruthie clucked her tongue while spinning the paddle around in an expert hand while glaring at the hunter. "Don't you be flip with me, Caleb," she snapped, sliding her eyes to where Sam was sitting in her office. "Fourteen year old boys are just a pile of raging hormones and you brought an inexperienced, scared, naïve fourteen year old boy in here and then left him while you went off with Sara Lynn! I should beat you until you couldn't sit down…if I didn't think you'd enjoy it!"

Swallowing the comment that came to mind, Caleb raised his hands and admitted defeat. "Dean treats him like a baby. His Dad ignores most of what Dean and I do but I know he'd never let Sam get within fifty feet of a place like this and I figured at his age then he should at least get to see a living breathing naked woman before he actually got out on his own for the first time," he muttered, shifting under the harsh look. "Okay, Dean set up rules and I hate rules so…"

"So you decided to scar a poor boy?" Ruthie rolled her eyes. "You steer clear of this place for at least a month until I forget this mess," she ordered, leaning into her office with a much softer smile. "Sugar? Your moronic bodyguard is back."

Sam pushed his slightly too long hair back out of his eyes and Caleb didn't miss the mixture of emotion that was reflected briefly on his face and decided not to mention that Sam's jeans were actually cleaner now than they had been earlier because he knew he was a walking dead man anyway without bringing up the reason.

"Hey, kid," he lifted his brows and wondered how much it would take to buy Sam off. "Sorry, I took so long. Umm, I…"

"You need to get lessons from Dean, dude," Sam finally muttered, giving the owner a shy smile and a quiet 'thank you' before giving Caleb a glare and walking past him. "At least when he ducks out on me and is gone for hours he comes back looking a lot better than when he left. Can we go home now?"

Blowing out a breath, Caleb ignored the final glare the woman shot him when he ran to catch up to Sam but the boy had already reached his car by the time he got out of the club.

Sam was the quiet one of John's sons. Ever since Caleb had first met the Winchesters it had always amazed him that Sam and Dean were brothers because they weren't so much alike in mood, look, likes, tastes, etc but as he got into the car it suddenly hit him that Sam was very much Dean's brother because he was shooting off waves of silent anger along with a few other emotions that Dean only did when pissed off.

"Alright, this didn't turn out like I planned," he began after a long silence but wanted to at least figure out how deep he was before they got back to the motel and Sam closed himself off. "I got too distracted and I'm not used to being responsible for someone else and I…kind of…forgot you were out there but…was it all bad?"

His arms crossed tight across his chest, Sam kept staring out the windshield for a long while before he slowly let out a breath much like Dean did when pissed at Caleb but willing to start to forget it. "What's all the toys for?" he asked suddenly, smiling a little when he felt the car swerve at Caleb's startled jerk. "I mean, all those dancers were…hot, I guess, and…once they took off the clothes…so why do they need that…stuff? Do you and Dean ever use…"

"Whoa!" Caleb felt his eyes go white before he could get control of his heart again, pulling into the motel lot but made no move to get out. "First, let's not ever use the words me and Dean in the same sentence while discussing sex toys," he managed to get out since while he was willing to try a lot of stuff that was something if even he'd want to Dean would kick his ass for the suggestion.

"No…well, I have but I'm pretty sure your brother doesn't and _please _don't ask him," Caleb could see the vein in Dean's face just pounding if Sam ever asked him that and it wouldn't take the older brother long to figure out who'd put it in Sam's head to begin with. "Not all the girls do. I just picked a really bad night to take you along.

"Sam, I figured take you out, show you some…hot girls, maybe let you work off some teenage angst or something while I worked off some angst but…I didn't know the more extreme girls were working tonight," he rolled his eyes while working his tongue around asking what he really didn't want to. "Umm, did anything…happen? You need to talk about…stuff or…?"

Stepping out of the car with his own set of motel room keys already in his hand, Sam leaned back in the car to shoot the hunter his best 'are you serious looks' before rolling his eyes. "Caleb, Dad and Dean both gave me _that _talk when I turned thirteen plus the schools these days actually have classes so I know all about what happened," he told him, dropping his voice a little. "I just would've preferred having Dean there, y'know?"

"Yeah, kiddo, I know," Caleb knew this should've been something Dean took care of but he still had his doubts if his friend would ever be able to see Sam as anything but his baby brother and if not then Dean's baby brother would not be seeing the inside of a strip club again in this lifetime. "You gonna tell Dean or John about tonight?"

"Dude, did that girl mess with you too much? I don't want you dead, Caleb and that's what would happen if either Dean or Dad find out," Sam knew this and decided that tonight would stay just between him and the other hunter…plus Sam wasn't foolish enough not to know leverage when he saw it. "Of course…I could slip up sometime or…"

Biting his lip from either laughing or cursing, Caleb saw another piece of Dean surfacing in the teen because his pal could angle and con with the best of them and little Sammy knew he had him by the short hairs because of this stunt.

"I've only got another sixty bucks on me tonight, Sam," he muttered, relishing his skin a lot more than his cash if that's what it would take to keep this quiet but frowned at the slight shake of Sam's head. "No? What then?"

"You convince Dad to let me come along on the next hunt he gives you and Dean," even though Sam really didn't like hunting he did enjoy spending time with his older brother and that's what it would take to keep this secret from his Dad and Dean. "A good hunt, Caleb."

Groaning because he knew how hard it was to convince the former Marine of anything, much less if it meant convincing him to allow him and Dean to take Sam anywhere if John or Bobby wasn't around but the determined look on the teen's face told him that he'd better be damn convincing if he didn't want skinned or lectured.

"Fine," he sighed, hearing the motel room phone ring and let out a breath when Sam snatched it up easily and just as quickly began a sniping match with Dean over the phone.

Slumping down on the couch to begin to figure out a lie to explain their nightly activities since he knew that Dean would be demanding an hour by hour accounting the second he was in the door, Caleb was just relieved that his brilliant plan didn't seem to have had any lasting effects on the youngest Winchester and he could put it behind him, never thinking about it again…

**2002, Palo Alto, California:**

"So, you finally got your own place?" Caleb was sipping his beer while staring down the blouse of Sara Lynn while she laughed and lifted his chin back so his eyes met her green ones.

"I've had this place for about three years," she waved a hand around her club which was going strong, especially on Friday nights with its all-male review. "Though you picked the wrong night to drop in to visit me…unless you've changed your tastes."

Swallowing the beer through a tight throat, Caleb closed his eyes while trying to ignore the beat from the stage behind him or the way the packed crowd of ladies seemed to suddenly scream as the new set began. "I always thought you were kidding about doing an all guy thing. Damn, those women are loud!" he winced as his head seemed to throb.

Sara Lynn's smile turned a little wicked while she ran a finger down his arm while leaning over the bar to put her lips next to his ear. "Probably got something to do with my newest dancer," she looked over Caleb's shoulder toward the stage. "He's got all the right stuff. Good body that still has that boyishness too it that the ladies love, long legs, long hands…and damn I still want to see what he can do with those hands. I told you he'd grow into those legs and hands, didn't I?"

Giving the soft suggestive phrase a smirk, Caleb took a drink of his beer just as those words hit home and he was between choking, spitting, and whirling on his stool toward the stage when once again he was nineteen and feeling like he was a walking dead man.

"Oh my God!" eyes now bulging out of his head, Caleb shook his head while rubbing viciously as his eyes as if to make the disturbing image on the stage just vanish when he looked again and decided he should just go jump off the Golden Gate Bridge on his way into San Francisco. "Sara…please tell me that is not who I think it is?"

Not wanting to but needing to be sure, Caleb forced himself to focus on the man on the stage and while trying not to notice that he really didn't look as nervous as he should have given what he seemed to be doing, he took a better look and bit his tongue.

Caleb hadn't seen Sam Winchester since the kid had left for college and while he'd gotten two different stories on the circumstances on Sam's leaving, he'd figured he'd go with Dean's since he'd seen how much losing Sam had hurt his friend while John was just silently raging.

Doing a mental timeline in his head, he guessed Sam to be around nineteen now and probably a sophomore in Stanford. He knew the kid was cut off from any contact with his family but Caleb also knew that Dean had been sneaking down here and slipping Sam money anomalously so finding him in a strip club…stripping to a bunch of women just didn't make sense to him.

"Sweet Jesus!" he nearly fell off the stool when he watched a young man he'd known since he was little do a slow strip tease while using that damn pole to do some very effective moves as he pulled off the pair of leather chaps to reveal what had to be the littlest scrap of black leather ever made.

Thinking back to the night he'd taken a fourteen year old Sam to a Texas strip club, Caleb knew this was karma paying him back and like the saying stated it was a bitch because as Sam reached for a toy out of the bag he'd laid beside the pole, the hunter knew that somewhere along the lines his best friend's little brother had learned the varying uses of that particular vibrating toy and whip.

"Sara…what the hell did you teach him?" he gritted, covering both eyes but peeked from between his fingers at a loud squeal from an older woman who had to be about eighty, one who had just shoved a bill down into the front of Sam's g-string. "No, no…he didn't just…God, help me. His brother will kill me if he finds out about this."

"I taught him a few things," Sara Lynn admitted, running her finger along her full bottom lip while watching Sam perform and smiling as a soft glean of sweat began to form in all the right places. "Of course, with his body and agility it was mainly the use of the toys which still made him blush. He's a natural to this though. Hell, I even suggested setting him up with a few people if he really needed the money," she sighed lustfully, green eyes going a little darker as the nineteen year old bent back while moving on the pole with the next toy in his hand. "He's perfect for so many…Caleb!"

Grabbing her wrist in a tight hold, that suggestion broke through to the hunter and he cut it off before she even went with it. "No," he refused firmly.

Seeing Sam dance like this was one thing since he figured there had to be a damn good reason since the boy he knew was a quiet reserved kid who'd blush red if anyone paid him too much attention. Thinking of Sara setting him up as a stud for any woman or man who'd pay…no, he'd be damned because he'd call Dean himself and risk his friend's temper.

"What…what's the reason he gave for this and how'd he even find you?" Caleb growled as one young woman got a little too touchy and wondered if he shouldn't step in for his absent friend because he was fairly certain Dean would've stepped in by now…after he killed him that is.

"I was handing out flyers in the park and Sam and his girlfriend came up. I never forget a face, especially one with a smile like his and the next day he came in to see me," Sara had known Caleb for a while and knew he was getting tense the longer Sam danced and the less he had on. "He said he was short about six hundred or so for something, rent, some books and such and would do this until he made enough. I figure between tips and what I pay, he'll probably just have to do this for another few weeks or…Caleb?"

Sam dancing, stripping to a room of women fantasizing about him for another few weeks? Oh, hell, no. Caleb dug into his wallet and felt a brief wince as he counted out his entire budget for this trip to the West Coast and just decided he'd be sleeping in his truck on this hunt.

"Here. After this…set, give him his pay, plus whatever the hell those grannies have been shoving at him plus this as a bonus for boosting your business and let him go," he told Sara Lynn, figuring that if Sam needed six hundred then the nine hundred he just plunked down would cushion his budget until either Sam could find a better job or Caleb got Dean on the phone and worked out a way to let him know his brother needed some help.

Sara Lynn seemed to hesitate over the suggestion of losing her best dancer but a hard grip on her wrist made her realize that Caleb was more than serious about this. "Fine, I'll give him his walking papers but I'll lose half of those women next week without him."

"He's a kid going to school, Sara," Caleb shook his head, looking back to see that the dance was finishing up and kept his eyes on Sam as he completed the show, offered a smile to the audience then stepped back and that was when Caleb saw it.

He'd been watching Sam to show the smallest amount of unease or to show some piece of the boy he'd been five years ago and finally as he stepped back out of the lights while another dancer stepped up he saw the way Sam's hands shook while he accepted a robe from backstage. 'There's the kid I know,' he thought before turning a final look at the hostess. "I check back next week, he better be gone," he warned in a tone he reserved only for those people he felt needed it. "He's out and got the normal he wanted so this stops cause, babe, I can promise that you do not want a visit from his big brother. Dean would level this place."

Waiting in the shadows of the kitchen, Caleb watched as Sara Lynn handed Sam, now fully dressed back in loose jeans and a worn sweatshirt, the envelope of money that he'd watched her put both his contribution and the normal pay plus tips in.

"This is more than what you told me you needed so I don't expect to see you back here again, hot stuff," she had to stretch onto the toes of her spiked heels to place a soft, but very chaste, kiss on Sam's cheek then laughed when he blushed.

Relieved that Sam would have the cash he needed without working at the club anymore, Caleb's fingers toyed on his phone for a long minute before giving up his life and hitting speed dial.

Listening to it ring twice before its owner picked up with a near snarl that told him that Dean and John must be at it again, he rolled his eyes while slipping outside to head for his truck to take a quick drive around the campus to be certain his favorite youngster was safe.

"Ace, you owe me money," he began in his usually cheerful voice, wincing at the reply and scrambling for a reply that could be plausible. "Remember that bet we made when you were seventeen? The one that said I couldn't bag a hag? Well, I'm out in Cali and you owe me…nine hundred bucks."

The choking made him smile and while he knew Dean would never come across with that he knew his mention of California would distract his friend into the question he knew would be coming. "Sam? Sam who? Oh, that Sam. Yeah, I swung through and…truth to tell, Ace…the kid's looking a little scrawny," he heard the sharp breath and knew he'd hooked his prey. "Seems he's…working a couple jobs to make ends meet and…what? You are? Well, if you want to come all this way…yeah, I'll see you then, Dean."

Hanging up the phone, Caleb leaned back in the cab while rubbing his newly shaved head with a cocky grin. "Winchesters, gotta love 'em…unless Dean finds out about this and that…then I'll be too busy being dead," he decided, knowing he had enough on his latest card for a room for the next couple nights and he'd make sure just want Sam was doing during the day and maybe check out the girl he's seeing just to be sure that she's good enough for Sam.

**2013, Men of Letters base, Kansas:**

"Sammy?" Dean knew his little brother was awake because he'd just had another coughing fit and Sam's chest still seemed to be rattling too much for his liking.

Keeping his eyes closed so his brother's bedroom didn't spin and he didn't lose whatever food he'd taken in that day, Sam swallowed then allowed the hand behind his head to help him lift it enough to sip whatever it was his brother decided he needed to drink. "Yeah?"

Getting Sam to sleep these days wasn't easy and when he did he would usually end up waking Dean up anyway so he'd just chosen to plant Sam's ass in his bed which was still big enough to allow his constantly moving brother the room to roll while Dean could still sit on the edge in case he was needed in a hurry.

"The other day back in Colorado when you brought up Caleb taking you to a damn strip club and you not knowing what they did on those poles until you were at school…did you…I mean, how long…damn," there was no way in hell that Dean could bring himself to ask if his little brother had actually stripped.

Easing one eye open enough that he could gaze at Dean from beneath long lashes, Sam nodded slightly then managed to grab for his brother's wrist to keep him still. "Just…did it…a few weeks," he mumbled, tired and aching now. "Needed cash for…rent…books…some food and I…didn't want Jess to ask her folks so this lady…um…I met gave me a job. She fired me after I made the money…though, I know what she was paying and the tips…umm, sorry but she said I earned a nine hundred dollar bonus for upping her business."

Forcing both eyes to open fully, Sam's tired and too huge puppy looking eyes stared at his brother for a long moment as if considering what to say. "I…didn't…want to do it, De'n but…just did it once and swore never again cause I told Jess…my big brother would kill me."

"Without a doubt, Sammy," Dean agreed, brushing a gentle hand down over Sam's face in a way to both make him grin and to mess up his hair like he used to. "Go to sleep, bitch."

"Jerk," Sam mumbled back before moving to his side but stayed close to Dean's side as if needing to know he wasn't alone.

Letting his hand stay on the back of Sam's neck, Dean slowly began to think back and that call from Caleb complaining about a bet and owing him nine hundred dollars came back and suddenly it all became very clear how his brother made the money and why he made it so quickly.

"_Sonuvabitch_," he whispered, letting his head rest back but kept his eyes open as if keeping watch that nothing entered his room or tried to hurt his brother. "Caleb, I am so resurrecting you just so I can kick your damn ass."

Dean had known that something was up with his friend when he joined up with him in Palo Alto a few days later, especially when Caleb had refused to let him near the one and only strip joint in that town.

Chuckling with a smile, he lightly squeezed Sam's neck. "There will always be someone watching over you, Sammy," he whispered, just hoping that still held true while struggling to scrub his brain clean of any images of Sam on a dance pole were giving him. "Damn it. That's almost as bad as him and Ruby."

**The End**

**A/NII: **_Everyone make it through it? Well, I'm glad. Thanks for reading and I hope you enjoyed it. Reviews are loved and please look me up on Facebook under morgana07 as I have a group to keep up to date with fans._


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